After a person pours their heart out to you in some sad story that you either do not care about or have lost interest in, a high-five is offered by saying "Aww, I'm sorry... self-loathing high-five?" that basically shows false empathy and lack of sympathy that the person is actually seeking, thus showing that the person has not only had a bad day but hates themselves as well.
Girl: "I spilled my lunch all over myself at lunch and while everyone was laughing at me, my boyfriend told me he was dumping me for another girl."
Boy: "That sucks. Self-loathing high-five?"
Girl: "Sure" (high-fives the person)
12 step recovery jargon referring to someone new who talks about how great life is, now that they'resober. Usually meaning that the person is out of touch with reality.
The new guy seems pretty happy for a dude who has no job, no money and no family. He must be on a pink cloud.